I should also add that I'm going to be going from NYC to Chicago first, then from Chicago to Toronto. So do I exchange at LaGuardia, O'Hare, Pearson, or a Canadian bank?

I never do my changes at an airport if I can help it. All airport rates are generally a bit higher and have handling fees. AND if I can, I always try to do the bulk of my exchanges in the foreign country as you tend to do a little better for rates. However, I try to have a little bit of foreign currency before I get to the country for the airport just in case (for taxis and food etc.)

U.S - Canada - Do you have time to go to a bank at home? This is the easiest way to change a chunk of money and probably get a decent rate. Otherwise, just change at Pearson. A Canadian bank might also charge you a handling fee if you don't have an account with them.

Oh, here's an anecdote:

In Hong Kong, where people travel a bit more since it is a hub and quite cheap, there are very competitive money-changing places. In fact, there is one whole street of them. My sister tasked me with changing money for our vacation and since we decided to pay the hotel in cash, I was changing a whole chunk of cash.

First of all, when I arrived at the money-changing street, despite the fact that there were dozens of establishments, there were only people at one particular establishment. Not only were there people, there was a crowd of people! The New Year holiday was coming up and everyone was going away and everyone was changing money. But they would only do so at that one place!

So, the locals must know something about the rates there, so I got in line. And by 'got in line', I mean I joined the disorganized throng and elbowed my way around, until I was more or less in a position to jump to an open cashier. It was pretty crowded and everyone was pressed up against each other. I was definitely worried about my little stash of cash. As everyone was jostling, a man with two big canvas black bags came up. Now, perhaps I am stereotyping, but he was a bit...erm...Asian gangstery. The crowd fell silent, and parted immediately. He went right up to a cashier who was miraculously free and then was buzzed in back to a room. As soon as the man disappeared in back, the crowd went back to its jostling and hustling for position as if nothing happened! The man left with his bags a few minutes later. The crowd parted again for him.

We were all waiting, when suddenly all the windows in the cashiers closed up. For lunch they said. And then the cashiers proceeded to eat their box lunches while sitting at the windows, looking at the crowd.
The crowd of course, jeered and made good-natured comments, providing running commentary on one man's progress on his chicken and rice. Finally, they finished their lunches and one by one the cashiers opened their windows again. When I finally did get through, the exchange rate was extremely favourable, crazily so. Thank goodness, because it took me 2 hours of waiting to change my money!!!

Also Toronto meet-up while you are here!

I don't know about Canada, but when I went to France I exchanged a small number of euros at my local bank, and hit the ATM while I was there. The rate was very favorable even including the ATM fee.

yeah use an ATM if you're going to be spending a bunch of money. if you're only going to be spending a little bit here and there, just use your USD . any store will accept it and the rate won't be unreasonable

Bank or ATM (or ATM at the bank, of course). I avoid airport exchanges as much as humanly possible.

Anytime I travel abroad I just take out cash from an ATM or used my debit/credit card to pay at the register. Your bank will probably charge a nominal conversion fee, but I think it's worth it for the convenience. And I'm under the impression that they're converting the transaction based on a live rate, instead of an average or something. But that's probably me just making things up about currency conversion.

And good job on getting the camera back to the wedding couple!

What I used to do was bring $200 in traveler's checks with me and exchange them at the bank nearest to the friend's house in Canada where I was crashing. I've budgeted about $150 for my entire stay in Canada, and what it sounds like would be the best thing to do would be to get $100 CDN from an ATM when I get there and hope the rest goes well, ne?

Which brings me to my second question, which is Canadian-specific: Most ubiquitous/best branch to look for? Also, go to the branch, or try the airport kiosk?

Do you need money for transit from the airport, or is someone picking you up?

If you need money for transit, there are ATMs in Pearson. I don't remember their fees being unreasonable.

If you don't need money for transit, then I'd just use an ATM at the airport if I had to walk by one anyway. If not, then have whoever's picking you up stop at whatever ATM is convenient to your travels.

IIRC, the fees and exchange rates will be comparable across banks, well under the point of it being worth caring about finding the best one. In the neighborhood of CAD2-4 per transaction, plus whatever your home bank charges. Unless things have changed in the past few months, Canadian ATMs don't have to disclose their fee amounts before the transaction. Anyway, just use whatever's handy, though I'd guess that actual-bank ATMs would be less likely to charge exorbitant fees than little convenience-store ones.